Azodyestuff



Patented Oct. 2, 1934 UNITED STATES" PATENT OFFICEQ 1,975,411 AzofiyE'sTUFF Richard Stiisser, Cologne- Denta Germany, as-

signor to GeneraF'Anili'ne Works, Inc., New a. v s'l -z fl a p om ro l wa e? c No Drawing. Application May;25; 1932, Sferial' No. g 613,559. In GermanyfJune-"I'Y,1931* f r Claims; (01. 2601-72) fI'he present'invention relates to azodyestuffs, ,more particularly it relates to dyestuffs which may be representedby the generalfformula:

wherein Rstandsfor th'e'radical of a diazotized aminoazodyestufi containing at least two azogroups that means, for the radical of a diazotized amin0dis-, -trisor -polyazodyestuff, R stands for the radical of a hydroXy-carbazolecom pound, the azo' group being attachedito R in ortho-position to the hydroxy group, n and n stand for the numbers one or two, but nandnf not simultaneously standing for two, and where- R.- may be substitutedflby'hydroxyl, alkoxy, aryloxy, alkyl, a substituted amino group -such as an acylamino group, thenitrogroup, halogen, the sulfonic acid group and the carboxylic acid group, and'whe'rein'R may be substitutedbyhydroxyl, alkoxy, aryloxy,-alkyl,-the amino group,

the nitro group,- halogen, the sulfonic acid group,

-stufi,a dark powder is obtained which dyes cotton and viscose silk g reylshades of good fast ness' 35 and the carboxylic acid group. a

My dyestufis are obtainable by dis-azodyestuif prepared fro-mlmolecular proportion of 1 diazotized 2-aminonaphthalene-4.8-- disulfonicacid, 1 molecular proportionof 1-;. naphthylamine and 1 molecular proportion of 3-amino-4-cresol-methylether are diazotized the usualmanner. Thediazodisazodyestufi thus obtained'is" filtered off and added, while stirring,

diazotizinggortetrazotizing a monoaminoor diamino-dis-orgy, -polyazodyestufi and coupling with. one: or two;

'toasolution of 343 parts byiweigh't of 1 -hydrox'y carbazo1e-3.6.-disulfonic acid in 4000 parts by v weight'of water, 200 parts by weightof soda pyridine and .some ice; When thecoupling is complet'e the dyestuif'is salted out and filtered;

The trisazodyestufi-having in its freestate the 50 following f ormulaz V is a black powder which dyes cotton, silk,-vi s= cose. silk and chrome leather greyish-blue to bluish-black shades of good fastness to water, light'and brightening. '1 r I Example 2.63'3 parts by weight of the aminodisazodyestuff prepared from 1 molecular ,proportion of diazotized z-naphthylamine 'l-sulfonic acid, coupled with l molecular proportion of: p=xylidine, further "diazotized and coupled with '1 molecular proportion of 'l-j'amino- 2-haphth'olethylether-fisulfonicj acid, are diazotized and coupled with358. parts byweiglit of l-amino? 8-hydr0Xy-carbazole 3lfi-disulfonic acid in the. presence of pyridine. Afterfworking upthe d'yeto light. The dyestuff has in its free statethe followingformula: j J

0H3 oozm 011' 7 NH:

Example 3. 184 parts weight of 4.4-diamino-diphenyl are tetrazotized in the usual mannen and coupled in a weakly acid solution 316-disulfonicl acid. The diazoazodyestuff thus obtained is then coupled in a. soda alkaline solution ,with 93 parts by weight of diazotizedaniwith 319:parts by, weight of 1-amin0-8-naphtho1- mama finally. the diazodisazodyestuff is cou- V pledwith 263 :parts by weight'of 2-hydroxyr-car- HOaS silk greenish-grey shades. In its free state the dyestufi corresponds to the following formula:

dyestuff prepared from 1 molecular proportion of diazotizedp-nitraniline, coupled in an alkaline solution with 1 molecular proportion of 2- amino 8 hydroxynaphthalene-6-sulfonic acid, which is reduced to the amino-azodyestufii by means of sodium sulfide, are tetrazotized in the usual manner in concentrated solution with 70 parts by weight of sodium nitrite and 350 parts by weight of hydrochloric acid of 19 B. While stirring, the solution is then added icecold to a concentrated soda alkaline solution of 716 parts by weight of l-amino-B-hydroxy-carbazole-3.6-disulfonic acid in the presence of some pyridine. After a short time the coupling is complete. The trisazodyestuff is salted out and filtered. After drying a black powder is obtained which dyes cotton, viscose silk and silk black shades of good fastness properties. In its free state the dyestufi corresponds to the following formula: H

OH OH wherein R stands for the radical of a diazotized aminoazodyestuff containing at least two azo groups, R stands for the radical of a hydroxy- 'carbazole compound, the azo group being attached to R in ortho-position to the hydroxy group, 12

and n stand for the numbers one or two, but n and n not simultaneously standing for two, and wherein R may be substituted by hydroxyl,

'alkoxy, aryloxy, alkyl a substituted amino group, the nitro group, halogen the sulfonic acid group and the carboxylic acid group and R may be substituted by hydroxyl, alkoxy, aryloxy, alkyl, the amino group, the nitro group, halogen, the

rious shades of good fastness to light.

sulfonic acid group and the carboxylic acid group, being generally dark powders, and dyeing vegetable and/or animal fibers and/or leather va- SOlH 2. The azodyestufls of the general formula:

I I :l RN=NR' wherein R stands for the radical of a diazotized aminoazodyestuff containing at least two azo groups, R stands for the radical of a hydroxycarbazole compound, the azo group being attached tdR' in ortho-position to the hydroxy group, n stands for the numbers one or two, and. wherein R may be substituted by hydroxyl, alkoxy, aryloxy, alkyl, a substituted amino group, the nitro'group, halogen, the sulfonic acid group and the carboxylic acid group, and R may be substituted by hydroxyl, alkoxy, aryloxy, alkyl, the amino group, the nitro group, halogen, the sulfonicacid group and the carboxylic acid group, the coupling components being selected in such a manner that at least one contains as substituent a sulfonic acid group, being generally dark powders, and dyeing vegetable and/or animal OH 1 1 NH: 9

HO S SOSH fibersand/ or leather various shades of good fastness to light. 7 l l 3. The azodyestuffs of the general formula:

g R" in ortho-position t0 the hydroxy group and which may be further substituted by an amino group and a sulfonic acid group, being generally dark powders, and dyeing vegetable and/or animal fibers and/or leather various shades of good fastness to light. ,7

4. The azodyestuff of the following formula:

OOH3 OH l 5140 H038 S03E77 being a black powder and dyeing cotton, silk, viscose silk and chrome leather greyish-blue to blueish-black shades of good fastness to water,

' light and brightening,

RICHARD s'riissER. 

